alpha,alpha-Bis(trifluoromethyl)-4-vinylbenzyl alcohol
[CAS# 2386-82-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: alpha,alpha-Bis(trifluoromethyl)-4-vinylbenzyl alcohol
• Synonyms: 4-(2,2,2-Trifluoro-1-hydroxy-1-trifluoromethylethyl)styrene; p-(Hexafluoro-2-hydroxypropyl)styrene
• Molecular Formula: C₁₁H₈F₆O
• Molecular Weight: 270.17
• CAS Registry Number: 2386-82-5
• SMILES: C=CC1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O

Properties

• Solubility: Very slightly soluble (0.12 g/L) (25 °C), Calc.^*
• Density: 1.379±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 77-78 °C (5 Torr)^**
• Refractive index: 1.452 (589.3 nm 25 °C)^**
• Flash point: 110.6±27.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

^** Middleton, William J.

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H225-H315-H319
• Safety Statements: P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235

Discovery and Applications

Alpha,alpha-Bis(trifluoromethyl)-4-vinylbenzyl alcohol is a unique organic compound distinguished by its trifluoromethyl groups and a vinylbenzyl alcohol moiety. This compound features two trifluoromethyl groups attached to the alpha position of the benzyl ring and a vinyl group linked to the hydroxyl-bearing benzyl ring. It is known for its distinctive chemical properties, which make it valuable in various fields of research and industrial applications.

The discovery of alpha,alpha-bis(trifluoromethyl)-4-vinylbenzyl alcohol began with studies on trifluoromethylated organic compounds in the late 20th century. Researchers were exploring the effects of trifluoromethyl substitution on the reactivity and stability of aromatic systems. The introduction of the vinyl and hydroxyl groups provided additional functional diversity to the molecule, leading to its exploration in multiple applications.

In organic synthesis, alpha,alpha-bis(trifluoromethyl)-4-vinylbenzyl alcohol serves as a versatile building block. Its trifluoromethyl groups enhance the electron-withdrawing properties of the benzyl ring, which can significantly influence the reactivity of the compound. This property is useful for the development of novel materials and molecules in organic chemistry. The compound can participate in various reactions, including polymerizations and cross-coupling reactions, where its unique substituents contribute to the formation of complex structures.

One notable application of this compound is in the development of advanced polymer materials. The trifluoromethyl groups contribute to the hydrophobicity and chemical stability of polymers, making them suitable for use in harsh environments. These polymers are often employed in coatings, adhesives, and advanced composites where durability and resistance to chemical degradation are critical.

Additionally, alpha,alpha-bis(trifluoromethyl)-4-vinylbenzyl alcohol is utilized in the synthesis of specialized functional materials. Its ability to participate in polymerization reactions allows for the creation of materials with tailored properties, such as improved thermal stability or enhanced electrical conductivity. These materials have applications in electronic devices, sensors, and other high-performance technologies.

In medicinal chemistry, this compound's structure can be used as a scaffold for the development of new pharmaceutical agents. The trifluoromethyl groups can influence the pharmacokinetics and pharmacodynamics of drug candidates, making it a valuable component in drug design and development. The compound's vinylbenzyl alcohol moiety provides further opportunities for modification and functionalization, allowing researchers to create diverse chemical entities with potential therapeutic applications.

Overall, alpha,alpha-bis(trifluoromethyl)-4-vinylbenzyl alcohol is a significant compound in organic chemistry and material science. Its unique chemical properties and versatile applications in polymer science, functional materials, and medicinal chemistry highlight its importance in advancing various fields of research and technology.

References

2019. Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More. Synthesis, 51(24).
DOI: 10.1055/s-0039-1690038